


Unexpected reunions

by Dasetho



Series: facing the past and shaping the future [1]
Category: Community (TV)
Genre: F/M, Post-Season/Series 06
Language: English
Status: Completed
Published: 2020-07-19
Updated: 2020-07-29
Packaged: 2021-03-05 06:26:59
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 18,151
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25379848
Author URL: https://archiveofourown.org/users/Dasetho/pseuds/Dasetho
Summary: “Go away dad… You had plenty of chances to explain”Annie is in DC when not only her Greendale-past but also her pre-Greendale-past decide to get involved in her life again.
Relationships: Annie Edison/Jeff Winger
Series: facing the past and shaping the future [1]
Series URL: https://archiveofourown.org/series/1837951
Comments: 18
Kudos: 53





	1. unexpected visitor

**Author's Note:**

> This is a prequel to "the fathers you can't leave behind and the lovers you can't let go" which I published as a one-shot but am now putting in the context of a multi-chapter story/series. Hope you enjoy it!  
> (Also sorry for any grammatical or spelling mistakes, I think I got them all but some always slip through. I should really find someone to read over these before I post them...)

The sun was setting after a warm day in DC. Annie had just finished her evening run and, in the best way possible, felt exhausted. She ran a good time today, personal best. A mark she was set on breaking tomorrow. She hadn’t been much of a runner back in Greendale. Having barely enough time to focus on all her College-related activities, she never got into sports and being active that much. But she really enjoyed how it was a way to challenge herself and be better every day which had become kind of a motto for her ever since she left for DC. 

Besides, getting into running was the perfect excuse to keep in touch with a certain someone more regularly. A certain someone who put little less than religious emphasis on the state of his own body and was more than willing to share a few of his secrets with her. And maybe she just liked to think that that certain someone also enjoyed hearing about her _physical prowess_ …or well…her body in general. 

Her thoughts were interrupted by her phone ringing in the pouch she had on her arm. Slightly annoyed at not only her train of thoughts but also her running playlist ( _Annie’s Run & Fun_ …the title was still a work in progress) being interrupted, she looked at her phone and lightened up instantly as it said ‘Jeff Winger’ on the screen. Taking out her earbuds, she quickly answered the call. 

“M’Lord” She said confidently, all to fondly remembering their little greeting thing that had started all the way back in her first year at Greendale. 

“Mi’lady” Him saying that hadn’t yet lost any of the effect it had on Annie, still bringing a smile to her lips as she casually strolled into her apartment complex. For the first week or so of her stay in D.C., Annie tried to think of Jeff as little as possible, out of fear that it would somehow cause a sort of relapse into a pool of feelings she didn’t want to tap into again, at least not so soon. But as the weeks went by, she became much more comfortable and relaxed about it. They had passed the really awkward phase after about two weeks and after that, they texted regularly and even talked on the phone once or twice. They talked mostly about random and completely non sentimental stuff like the newly released running shoes or how her internship was going or how his students drove him mad. And she didn’t talk to him any more than she did with the other members of the former study-group. But not any less either. And after everything that happened between them, especially their goodbye-kiss, that was more than she could really ask for. 

“So how is Greendale’s best and only chance of producing an actually successful graduate doing today?”

She chuckled at his remark, knowing full well that it was meant mockingly but also carried the slightest bit of pride in it. “I’m fine, thanks! How about Greendale’s shoe in for teacher of the year?” 

He laughed at the comment and sarcastically replied. “I don’t know, I’ll ask Duncan when I see him”

“Jeff Winger, not accepting a compliment? Didn’t think I’d see the day…” she was glad that they could have casual exchanges like this. 

She liked to think that he was in a good place right now mentally. But sometimes she couldn’t help but remember the strong façade that Jeff had perfected over the years and she wondered if in those casual text-messages and phone calls, he was really feeling a lot more than he led her to believe. She tried her best to not read too much into their exchanges. He did say that he let her go after all. But it wasn’t always easy to just ignore some phrases he used that _might_ be hinting at something or some questions he asked that _might_ have an ulterior motive behind them. But it’s not like she’s actively picking those snippets of text messages and conversations out to reflect on them extensively…at least that’s what she was trying to convince herself of. It worked most of the time.

“Not exactly sure if Greendale’s teacher of the year is a real compliment… Though if you really wanted to complement me, you should focus on other parts of my personality. Like my irresistible charm…or my abs.”

She rolled her eyes at his arrogance “Abs are not part of your personality Jeff…and your charm is not as irresistible as you think!” 

Not giving her the satisfaction of being offended by that, Jeff instantly tried to convince her otherwise. “First: they are if their as spectacular as mine, second: don’t even pretend that you weren’t affected by my irresistibleness too at some point”

She was glad that he couldn’t see her cheeks reddening ever so slightly. The way this conversation was going could almost be considered…flirtatious. But two could play at that game…

“You wish! The last time I remember seeing you, it was rather the other way around wasn’t it?” 

There was a short moment of silence. It was just long enough to make her question if she went too far, but not long enough to put real concern in her mind.

“You’re cute alright? But you still got some way to go with your running routine before your body can match up to mine”

She was relieved that her little dig didn’t hurt his ego too much or stirred up unwanted feelings. Now confident that this little flirty thing they had going on here wasn’t harmful after all, she continued to challenge him.

“So you want to compare bodies huh? Think I can’t hang with you… _old man?_ ”

He audibly gasped at her cruelty. 

“Ouch! Uncalled for! Totally uncalled for! Besides, you know full well that even when I’m sixty, my abs will still be spectacular, and you would still ogle me every chance you get…”

Now it was her turn to gasp or rather gag at his words.

“Eww! Jeff! Gross! I would NOT ogle at a 60-year old…even if he had your abs”

She could tell that he somewhat doubted that that was really true.

“You keep telling yourself that Edison, you just keep telling yourself that!” 

She sighed and shook her head as she walked into the corridor on the third floor of her building. Her apartment was just around the next corner. 

“Imagine me rolling my eyes right now ok?” 

“Don’t have to” he quickly answered. “I could basically hear them” 

Relieved that their call was taking a slightly less weird turn now, she remembered what she wanted to ask him over the last few days.

“Well maybe you want to see them as well. I was thinking of organizing a Skype call with the group”

Although he was audibly excited about the suggestion, his reply still sounded smug as hell.

“Sounds great, then I can finally check out your new apartment and judge for myself if you’ve made something out of yourself that I can be proud of”

Annie could only shake her head at that remark.

“ _See if I’ve made something out of myself you could be proud of_? Please… you know who you sound like right now?”

“If what you’re about to say makes me feel old I will never forgive you!” Jeff was trying his best to sound more worried than amused. He failed miserably.

“Jeff! You’re not that old” She lulled him into a false sense of security before hitting him with the punchline. Which, unlike her class on how to write Jokes led her to believe, is actually essential.

“But…you know…theoretically speaking…” 

He tried his best at stopping her in her tracks. 

“Annie…I’m warning you…”

But, jokingly or not, she set her mind on hitting him where it hurt…  
“I mean…looking at our age gap…”

“Don’t say it Annie…”

“you could be considered old enough to…”

“Annie, I will hate myself…”

“..to be mistaken for my…”

“ANNIE NO!”

“…”

The word got stuck in her throat. Not because of Jeff’s totally overdramatic reaction, or because she felt a sudden rush of pity and regretted her attempt to playfully make him feel old.

Not because of her thinking it might be inappropriate to compare a man she _passionately_ kissed several times to a close family member. 

It was because of what she saw or rather who she saw standing in front of her apartment door when she walked around the corner. 

It was because now, as that man was looking her right in the eyes and she looked back into his which bared a slight but unmissable resemblance to her own, she could no longer speak the word. 

At least not in a comedic way, as part of a joke. Because she said the word alright, but there was nothing funny about it.

“…Dad?”

“Hello Annie…”

\--------------------------------------------------------------------------

“Annie?...Annie are you there?...Are you alright?...”

If this was part of the joke, Jeff really didn’t get it. He remembered that time she told the group about the Joke-writing class she dropped after the lesson on set ups, but he would have thought that by now, Annie would have learned that a joke doesn’t end there.

Maybe the connection was bad? It would be weird as they never had any problems with that ever since she left, but totally possible. Jeff was just about to hang up and call again later, when he finally heard her say the word that he had been expecting almost a minute ago. 

“…Dad?” 

More than a little bit confused at her sudden change of tone, he wasn’t sure how to reply.

“uhm…Oh no? Take it back?...Annie you really need to work on your-“

He was cut off by the sound of her hanging up. Which had him quite worried. It wasn’t like her to hang up like that. ‘There must have been a problem’ he thought to himself, instantly going through all the possible scenarios, ranging from a connection problem to her being kidnapped. Though the latter would definitely be the worst timeline…he had spent too much time with Abed.

He tried calling her again, but she didn’t pick up. He did that two more times before giving up and throwing his phone on the couch. With a sigh he fell back onto the cushions and ran a hand through his hair. 

Had he said something wrong? Had she realized in the middle of her joke about his age, that it actually did bother her a lot? Would she even want to speak with him again? Was he even worth speaking to? Was he even worth the air he was breathing? …wow, that went dark fast. 

She always did this to him. Had this happened with anyone else, then he would have just shrugged it off without wasting another second thinking about it. So she unexpectedly hung up on him, it’s not a big deal right? Except that with Annie, it really was a big deal. To him, anything concerning Annie was a big deal. And most of it led to him having to tell himself that he was fine with her leaving. Which he knew was a lie because he simultaneously had to shut out the little voice in the back of his head that tried to get him to jump of a cliff if he didn’t see her again soon.

With what little was left of his energy for the day, Jeff slung himself off the couch and made his way to his kitchen cabinet. He grabbed a bottle of scotch and a glass, pouring himself a generous amount. He really would have liked to talk to Annie a while longer this evening, but since he couldn’t have that apparently, the alcohol had to keep him company instead. It had been like this ever since she left, but he only realized it maybe one or two weeks ago. 

Every time he felt down, he would do one of two things, talk to Annie or go straight for the bottle. He knew it wasn’t healthy. In fact, he was certain that it would become borderline destructive before long and that he shouldn’t be that dependent on either of those things. But today was not the day to change that. And if he was being honest, tomorrow probably wouldn’t be that day either. So he took a sip of his scotch before walking back into the living room.

He turned on the TV and switched through the channels, finally settling on a rerun of friends. He didn’t actually like the show that much. But – and he would never admit this openly to anyone – in a pretty pathetic way, it gave him hope. _‘I mean, if friends as close as Monica and Chandler, or Ross and Rachel could get together, then it could probably work for… NO.’_ He could not go down that road again…

Only the slightest thought of it immediately brought back that memory. The memory of that bitter-sweet moment he had shared with Annie. The night where he kissed her goodbye. The night that he let her go. He knew it was the right thing to do…but that didn’t make it any easier for him. He knew that she was meant to go out into the world and put her mark on it. And he knew that he was not the one to be by her side when she did. He knew that it didn’t matter how much he would have tried to support her. Being in a relationship with someone as washed up and broken as him was a burden he couldn’t put on Annie, when she still had to learn and achieve so much in her life. He knew all this. But knowing is one thing. Accepting it…living with that knowledge and all its consequences…that’s a different thing entirely. 

He shook his head in disappointment at his own inability to let these thoughts go, thinking to himself that he should probably just call it a night and go to bed. He picked up his phone from the couch and took a sip of his scotch, preparing to write a text-message to Annie informing her that she could just call him back in the morning. And it was seriously something he had to prepare for mentally. There were several close calls over the last few weeks of him almost sending her half a romance novel, explaining in great detail how much he loved her and all the things he was willing and motivated to do for her…sometimes even the things he wanted to do to her. But even his drunken self was always capable enough to prevent those texts from being sent and possibly ruining the little bit of joy he had left in his life. 

The drunk dial him and Abed constructed for Britta all those years ago was a lesson he wouldn’t forget in this lifetime. And as if summoned by his thoughts, Britta totally britta’d his attempt of writing a text-message by calling him in that exact moment. He reluctantly answered the call, knowing that she would call him at least nine more times if he didn’t.

“You got the wrong number”

“Very funny Winger. You know, I think you used to be a lot wittier in your younger years”

He didn’t need to fake annoyance this time. He liked these digs at his age much more when they were coming from Annie…

“You’re the worst Britta…which is something that hasn’t changed since your younger years”

It didn’t seem to have the effect on her that he thought it would have. She actually sounded even more smug than before.

“Well…I guess I can be…so I guess you don’t want your birthday present anymore, seeing as though you would get it from _the worst_ ” 

He didn’t even try to hold in the laughter. Only Britta could be so misguided when trying to sound smug.

“Britta…I hate to kick you of your high horse – oh wait I actually love to – but even you’ve got to know how way off you are if you think you can give me a birthday present in the summer…”

Britta fell silent for a few seconds. He could only assume that she was coming up with her best attempt at a clever comeback.

It was a sorry attempt. “well…it’s a belated birthday present” 

“It’s actually an early one if we go by which is closer” Jeff replied with his laughter now turned down to a light chuckle. 

Having found some new confidence in her next approach, Britta came up with a different proposition.

“So…seeing as it is not your birthday, maybe you are still interested in the ticket. You could buy it off me you know, it would be a lot cheaper for me than cancelling it completely”

He rolled his eyes at this. She couldn’t possibly think that he would be interested in some event-ticket that she picked out.

“I’m sorry, but I’m not really interested in going to a rage against anarchy system corporate America thing or whatever”

She was obviously a little confused judging by the returning silence but caught up quickly and turned to what was surely her favorite activity: correcting him.

“No Jackass, flight-tickets. I want to offer you a trip to DC and back”

Now it was his turn to fall into more than a couple seconds of silence. Did he hear that right?

“Hello? Earth to Winger, are you still there buddy?”

‘okay’ he thought to himself. Play it cool now. He knew he should decline. There was no way he could fly after Annie less than two months after she left. It would seem desperate. And it would kind of destroy the whole purpose and intention behind letting her go. But maybe it would be good seeing her. Their conversations over the phone were pretty casual after all, and maybe the unresolved tension between them wouldn’t be such a problem….okay who was he kidding, there is no way that seeing her now would send his heart and brain into overdrive and probably far beyond that into actually life threatening spheres. There was no way he could take the flight…right?

“Well Jeff, if you don’t want them I can just-“

“-NO!” Way to play it cool Jeff… “I…I’ll take them” His inner self could strangle him right about now.

“Great! You can go see the sights, maybe take advantage of all the beautiful running routes, learn a bit about our countrie’s brutal and patriarchic culture…and something else…gosh, what was it again…”

Jeff knew full well what was about to come, but he had already surrendered his dignity in this call and saw no point in fighting for it any longer. So he just let it happen.

“I guess you’re talking about An-“ 

“ANNIE! That’s right” Brittas voice bellowed triumphantly through his phone. He had to give her this victory. God, she really was the worst.

“So when is the flight?” 

“Hmm? Oh yeah right, the flight…uhm…so you know how I always wanted all of us to be more spontaneous?” 

He didn’t have a good feeling about this. This whole situation is terrible, but the way she phrased that sentence made him fear for the worst.

“Britta. When. Is. The. Flight.”

It seemed like she was bracing herself for the worst because he almost couldn’t hear her through the phone.

“…its tomorrow”

He took a pause and breathed in sharply. His next words were very well thought out and carefully selected.

“WHAT THE HELL BRITTA!?”

“…at eight in the morning…”

“WHAT!?”

“I’ll drive you there ok?”

“THAT DOESN’T MAKE IT BETTER!!”

“pick you up at six?”

“BRITTA LISTEN!”

“alright, see you tomorrow”

“NO WAIT!”

“…click…”  
…  
Jeff was stunned into silence. At least that’s what it would seem like from the outside. Because inside his head, it was anything but silent. There was a storm, an earthquake and a tsunami raging in there at the same time. The remaining taste of scotch on his tongue felt like nuclear fallout and his brain started to shut down and delete its own existence.

_‘Oh crap…what have I done’_

\--------------------------------------------------------------------------

“What are you doing here!?”

Annie was actually shocked herself at how harsh those words sounded as they came out of her mouth. She couldn’t even process what was happening inside her right now. ‘how could her father be here? WHY is he here?’

“Look Annie-“

She didn’t let him finish. “NO! NOT ‘LOOK ANNIE’ OK!? You have about five seconds to explain why you’re here, and then I want you to leave!”

Visibly taken aback, not expecting to be greeted like this, her father took a moment to carefully choose his next words.

“Annie, I’m sorry. I’m sorry about everything. Can we please talk?” His look was caring and decisive. He clearly meant what he said, but that didn’t really make it any better in her mind.

“That’s not an explanation. And we have nothing to talk about, so just leave ok?” She said with tears starting to form in her eyes. _‘crap’_ she thought to herself. She could not cry in front of him. She couldn’t show any weakness. She didn’t need him. Never did. 

“Annie please…just give me ten minutes, I’ll explain everything I can” His voice cracked slightly, and he looked like he was clinging to the last lifeline he had left. But Annie wasn’t about to give him the benefit of the doubt.

“Go away dad… You had plenty of chances to explain”

“Annie-“

“I don’t want to hear it!” Her voice was now trembling, and she couldn’t hold back the flow of tears streaming down her face. “I’m going into MY apartment, and I don’t care what you do ok? As long as you’re gone when I open this door the next time!” 

Her father speechlessly looked on as she entered her apartment and slammed the door shut behind her.

Once inside, Annie slumped down onto the ground and sat with her back leaned against the door. Crying. She didn’t care anymore that he was probably hearing her through the door. She didn’t care about anything. She just wanted him to leave. The knock on the door didn’t even get a reaction from her.

“Annie…” Her father’s voice sounded weaker than before, as if he had given up. She could barely make out his words through the door. “…I can only imagine how you must be feeling right now. I’m really sorry Annie, about everything. And I understand that you don’t want to talk to me right now. But I’m leaving you my phone-number” A small piece of paper was passed underneath the door. “I really hope you give me a chance Annie. I know I can’t just make things right again like that, but whenever you’re ready…if you’re ready, please call me alright?”

Not willing to answer his question, she looked at the digits on the little post-it that her father had pushed under the door. She stayed quiet until she could hear footsteps from the hallway, slowly fading away in the distance.


	2. Unexpected visitor II

**Summary for the Chapter:**

> “Now go surprise your _not-girlfriend_ before someone else beats you to it!”  
> Jeff arrives in DC without a plan on how to approach Annie, who has her own problems, as she is trying her best to deal with her father suddenly reappearing in her life.

“God Shirley, you don’t know how good it is to hear your voice”

“Aww, I know, I got the voice of an angel” 

Only Shirley could pull of this blend of arrogance and friendliness that always left Annie wondering if she should be mad at her or thank her for her mere presence.  
But she had a point, hearing Shirley’s voice instantly lifted Annie’s spirits. The woman had always been someone she could turn to when she was feeling down or having trouble. And after Annie moved to DC, that bond got even closer to the point where they would talk on the phone almost every other day. 

Annie wanted to call her right after her dad had left yesterday, but she decided to wait a day and reflect on the situation on her own at first. But all she came up with in the end was even more confusion and anger.  
Which is why she cut the pleasantries and casual exchange short this time. She usually loved to hear about Shirley’s life and all the tales she had to tell about Mr. Butcher and her boys and Annie knew how much it meant to her friend that she actually listened to her. But today, she couldn’t ignore the one thing she had on her mind for very long and less than three minutes into the call, she told Shirley what it was really about.

“Shirley…I’ve got to talk to you about something, I hope it’s not a bad time right now”

“I always have time for you Annie, someone’s got to make sure you turn out alright” Clearly sensing that this was a about to be a serious conversation, Shirley changed to a more supportive tone. “So, what is it you wanted to talk about?”

Annie had thought about how to best approach the subject, knowing that Shirley had a rather strong opinion when it came to divorce and husbands leaving their wives. But she hoped that that would just mean that the woman would be more understanding of her situation or offer a different perspective at least.

“Well…I kind of met my father yesterday. Or…I guess ‘met’ is not the right word, he showed up unannounced and I told him to get lost” 

“Oh Annie…” Shirley paused for a second, probably needing a moment to process what she had heard. “That can’t have been easy for you. But I’m glad you stood up for yourself” 

Annie was grateful that Shirley didn’t hesitate to completely take her side in this, but her voice was still shaking a little as she continued to open up. “I don’t know if you can call it that really… I just… I just acted out to be honest. When I saw him I…” She felt a single tear making its way down her cheek “It was like I was ten years old again, and he was trying to buy me ice cream as an excuse for not making it to my school play” 

“I’m so sorry” The empathy in Shirley’s voice was unmissable. “Annie you don’t owe that man a thing ok? This man has been out of your life for ten years, doing lord knows what in the meantime! I know Jesus taught me to forgive but that ain’t no excuse for your father to just leave and come back as he pleases. And he’s Jewish anyway!”

“I know, that’s what I thought as well!” Annie said enthusiastically, before processing how Shirley had ended her sentence. “apart from the Jewish thing obviously…”

“…sorry”

“It’s ok” She decided to look over that for now “I know I don’t owe him anything, but that’s what bothers me so much. I don’t get why he would be here now. I don’t understand what makes him think that now is a good time to just show up again”

“Annie-“ Shirley tried to get a word in, but was immediately cut of by Annie, who was just getting started.

“He could have been there a long time ago! But I had to do it all by myself for all these years! No one helped me through school, no one helped me through my teenage years, when everything started to become…confusing. I had to do it all by myself, and I made it work ok!?”

“Annie-“

“If he really cared, he would have been there for all the crap I went through!”

“Annie-“

“He would have been there when I went to rehab, supporting me. He would have been there when I overcame my addiction, telling me how proud he was. And he would have been there when I went to Greendale. But he wasn’t…”

It was only after she finished her rant, that Annie remembered to breathe again. She was almost hyperventilating at this point and the single tear she felt before had become a steady stream, reddening her eyes and leaving salty trails as they fell from her face and dampened her carpet.

“Annie…” somewhere along Annie’s hate-filled speech, Shirley had started to cry as well. “Annie I never knew you felt this way. I…excuse me…” Annie could hear her friend shuffling through a bag. “I’m sorry, I just…needed to get some tissues” 

After a few seconds, Shirley started talking again, still a bit shaky and sniffling occasionally. “Annie I’m so proud of you. And I’m glad you told me all of this. You can always come to me if you have to get something of your chest alright?”

Annie nodded instinctively before remembering that Shirley couldn’t see her. “Yes, I know. Thank you Shirley, I…I feel better already” 

“Anytime” Judging by her tone, her mood started to lighten up again as well. “Annie you know I love you like a daughter. And I will always support you no matter what” 

Shirley hesitated shortly before saying her next words with clear emphasis. “Because we are family Annie. And that’s what family is there for!”

\----------------------------------------------  
“Here you go” 

Jeff looked up from his phone as the bartender set his drink down before him. The room was filled with people, so he felt lucky to find a place right by the bar and sat down next to a 60-something year old in a grey jacket who wasn’t paying him much attention as he was instead focusing on an almost empty glass before him

“Thanks” he murmured, half to himself, not even sure if the woman behind the bar had heard it. 

He took a sip from his scotch, letting the smooth tingling sensation dull his senses. He couldn’t do this. He couldn’t see her.

He had landed in DC on time and thought about driving straight to Annie’s place, but decided against it, arguing that she was probably out somewhere until the evening. Or at least that’s what he told himself was the reason for not seeking her out right away. It was definitely not the suffocating feeling that had kept him up all of last night. 

So instead of seeing her, he took a cab to the hotel where he had booked a room just last night, being endlessly thankful for the fact that he found a place to stay on such short notice, because there was no way he could ask Annie if he could stay at her place for a week. He could barely muster up the courage to just go and talk to her as it is.

And so he ended up at the place where he was currently at: a bar right next to his hotel where he went after dumping off the little bit of luggage he had brought with him.

He couldn’t do this. He just couldn’t. What if she doesn’t want to see him? What is he even going to say to her? _‘Oh hey Annie! I’m sorry if I’m interrupting your new life or destroying any sort of personal development you might have been able to achieve over the last months, but I was actually wrong about that whole ‘letting you go’ stuff and I need to be with you and ruin your life for my own selfish reasons. Hope you don’t mind!’_ …yeah. He would need a lot more scotch to deal with this.

Unfortunately, his nerves even prevented him from fulfilling that desire correctly as he accidentally knocked his glass over when trying to go for another sip. The liquid ended up directly on the white shirt of the old man sitting next to him. 

“What the- “

Jeff needed a moment to process what was happening. His cognitive functions being just as dull right now as his coordination. 

“I…I’m so sorry…I’ll get you a towel or something”

“Hm, don’t worry about it” the man said while grabbing some napkins of the bar and cleaning his shirt. He had looked older from the side, but Jeff would still guess that he must at least be in his late 50s, based on the short grey-blackish hair and moustache, wrinkles on his forehead and the jacket which, while somewhat stylish, looked like it can’t have been made on this side of the two-thousands. “wasn’t going anywhere else today anyway”

The reassuring smile he gave Jeff calmed him down a bit. The last thing that he needed on this day was an actual barfight. In his current state of mind, he wasn’t sure if he could have controlled himself if it came to a confrontation.

“Look, I can pay for it, not sure if you’ll be able to get those stains out completely” Jeff said, remembering how years ago, he had to throw away some trousers that Alan had accidentally spilled some whiskey over at an office party.

The man waved him off and chuckled lightly. “thank you, but it’s alright, really. I wanted to throw this shirt out anyway, it’s probably older than you”

Jeff smiled at the remark. He wasn’t sure if he just felt guilty for spilling his drink on him or if it was something else, but he liked this guy. He never really got behind the whole ‘respect your elders!’ thing. In fact, he’s pretty sure that that was made up by people like Pierce or his Dad, who couldn’t contribute to society in any way and still wanted to be respected for something. But this guy seemed decent enough. So he came up with another proposition to make up for the ruined shirt, one which also had the benefit of giving him some extra time and some extra alcohol before meeting Annie.

“Let me buy you a drink then, have to put another order in anyway” he said while pointing at his now empty glass. 

The man sitting next to him looked surprised, but ultimately nodded in agreement. “Sure, won’t say no to that”

Jeff gave the bartender a sign, and after a minute or two she came over with another two glasses of the same scotch that Jeff had just spilled all over his drinking companion. 

“name’s Jeff by the way” he said while holding out his glass. 

“David” the man replied and clinked Jeff’s glass with his own.

After taking a sip and expecting the glass, Jeff was surprised to hear David critique his choice in whisky. “Always been more of a Lagavulin man to be honest, but I can see the appeal in good Macallan”

Not to be outclassed as a whisky connoisseur, Jeff accepted the challenge. “I guess I could live with a Lagavulin, but I think I’d rather smoke a Cuban cigar than my whisky”

“so you can’t handle the smoky flavor hm? Guess you still have some scotch to drink before you learn kid” the older man answered, visibly enjoying the conversation at this point. “but I won’t decline a Cuban cigar if that’s what you’re offering”

Jeff replied with a slight chuckle and a not so slight concern about his bank account “That would have to be one very expensive shirt you’re wearing for me to feel that guilty” 

They talked for a little while longer about favorite whisky brands, before moving onto sports and other random stuff. Jeff felt at ease talking to David. It was kind of nice to have a relaxing and meaningless conversation before meeting Annie and probably having to experience the polar opposite to that. 

“So are you from here?” Jeff asked while swirling around the last few drops of scotch in his glass.

“No, just visiting a…relative here”

Jeff picked up the little bit of hesitation in David’s answer. 

“Not looking forward to it?” He asked, thinking about how little contact he had with his own relatives.

David shook his head. “I actually met her Yesterday. It didn’t go too well… Which is what led me here” His look was difficult to read. Jeff thought about pursuing the topic further, but ultimately decided against it. Instead opting to go for his scotch again, emptying the glass in the process.

“Want another one? I’ll pay this time”

Jeff seriously considered taking David up on his offer but thought better of it in the end.  
“Thanks, but I’m good. I’m meeting a…friend later” It was right then when it hit Jeff again that he was about to see Annie in like an hour or so. He immediately tensed up and his mouth went dry.

“You alright?” 

“Yeah…it’s alright” Jeff cursed himself for being so obviously nervous. How the hell was this supposed to work when he actually saw Annie in person later?

David didn’t seem convinced, and Jeff couldn’t blame him, acting had never been his strong suit, and now he apparently wasn’t even capable of talking his way out of a situation either.

“When are you going to meet that friend of yours then?”

Frightened for a moment that he had spent way too long in this bar, Jeff looked at his watch and saw that it had just hit 7:00 pm and he suddenly remembered that he had been up for over 30 hours at this point. “Actually, we haven’t really set a time. She doesn’t even know that I’m here to be honest” He tried to sound at least somewhat indifferent but couldn’t pull it off at all.

David gave him a knowing smile. Clearly not having missed the change in tone when Jeff started talking about the girl he was about to surprise “Oh, that kind of _friend_ huh? Well, I bet she’ll be delighted to see you”

“I’m not so sure really…” Jeff’s lack of confidence started to actually embarrass him now. He used to command any room he entered back in the day. Now the mere thought of Annie had him doubting himself in front of what was little more than a stranger. ‘god I’m pathetic’ he thought to himself.

He flinched a little when David patted him on the shoulder and gave him a reassuring look. “Look Jeff, I’ve only met you an hour ago, but you seem like a great guy. I mean, most people your age would have just ignored an old man like me, no matter what and how much they spilled on them. Now I don’t know that girl of yours, but I’m willing to bet that you’re going to be just fine alright? Whatever it is you’re worrying about; it’s going to be alright”

Jeff looked up at him and nodded slightly. “You’re not that old” he said, trying to regain some of his wits.

“And you’re not that young” David’s remark stung a little, but Jeff just assumed that it was all in good fun. “And you’re also not getting any younger, so stop wasting time, drinking scotch with an old-timer like me. You should already be at your girlfriend’s doorstep with flowers in your hands”

Jeff would have appreciated the motivational speech had he not been hung up on one particular word in the middle of that phrase. “She’s not my girlfriend…”  
“Not with that attitude” David replied with what could almost be considered a touch of sass in his voice. “Now go surprise your _not-girlfriend_ before someone else beats you to it!”

\-------------------------------------

_‘Because we are family Annie. And that’s what family is there for’_

Shirley’s words from earlier resonated in Annie’s head as she fluffed her overly large pink pillow before resting her head on it and pulling her blankets up to her chin. At several points in her move to DC had she thought about getting rid of her pillow and blanket collection in favor of something more…mature. But she ultimately decided against it, arguing with herself that yes, she wanted to become more of a grown up, but that growing up is also a process, that should be taken step by step… and maybe she also just liked fluffy pink pillows, it’s not like there was anyone here to judge her. 

Plus, all the mementos she had from her old apartments always brought back good memories of her time in Greendale. Of her friends- no, her family. 

Because Shirley was right, they were a family. 

Shirley had always been a better mother for her than her real one ever was. Religious fanatic or not, Annie was sure that Shirley would have supported her through rehab, instead of forcing herself to ignore the issue altogether. 

Pierce…well Pierce might have been a racist maniac at times, but he cared about her most of the time. And he really wanted her to succeed, just like a good father – or in his case more of a grandfather - would. 

Troy and Abed were better brothers than she could ever dream of. Of course, they annoyed the crap out of her at times, back when she was living with them. But they were always there for her when she needed them. They always had an open ear, they always tried to help her when she was feeling down. And she actually enjoyed that she needed to take care of them at times. It made her feel more mature and she was proud of the fact that Troy and Abed non-ironically respected her and listened to her when she had something to say. 

Britta was the big sister she never had. Always listening, always trying to influence her in the best way possible and while her idealism and well…britaness could be a tad too much at times, Annie knew that the woman had her back and that she could always go to her when she needed to talk about… well anything basically.

And Jeff…well, Jeff was something else.

Before she could think about him any longer, there was a sudden knock on her door which almost made her jump out of bed. She looked at the clock, it was 9:00 pm. She had gone to bed a little earlier than usual, because she basically hadn’t slept at all the night before, but she wouldn’t have expected visitors at this time either way. At first, she thought it might be a neighbor, but they had mostly left her alone since she moved in, and she couldn’t think of a reason why one of them would want to talk to her this late. Then she started to panic a little when she thought about the possibility that this was her father again, but it wouldn’t make sense for him to show up again so soon, especially after he left her his number anyway. 

Whoever it was had clearly no intention of leaving as Annie heard the knock again and decided to get up this time. She considered throwing on some more clothes for a second, as she was only wearing very short yoga shorts, and a thin tank top. It had gotten quite hot in DC over the last week or so which is why she usually slept in what was basically little more than underwear, it’s not like anyone was there to watch her. And whoever it was that was knocking at her door would just have to deal with it.

The person knocked again before Annie could make her way to the door and she already prepared some harsh words in her head that she would throw at whoever that was, if she wasn’t satisfied with the reason he or she had to disturb her this late.

With one hand on the door handle, she took a deep breath and prepared for the worst, just in case it was _him_ again. With one quick motion that was way more sudden than it had to be, she swung her door open and looked at the person standing on her doormat. It wasn’t her father. But she was still glad for preparing herself mentally. It might have helped her even more with the man that was actually standing in front of her right now. Because with roses in his hands and a smile on his face that said more than a thousand words could possibly describe, the person standing in her doorway was none other than Jeff Winger. 

“Mi'lady…”

**Notes for the Chapter:**

> Hope you enjoyed the second chapter!  
> I know there hasn't been any real interaction between Annie and Jeff yet, but I wanted to really show where they are mentally, when they finally meet each other and I might have gotten a little carried away with that...  
> The next chapter(s) are going to mainly focus on the interaction between them, so I hope you'll check those out as well. I'll probably upload the next one tomorrow or the day after that.  
> Please leave feedback in the comments, because I really want to improve my writing and reading what you liked or didn't like is the best way to do that!


	3. how to mess up a basic 'hello'

**Summary for the Chapter:**

> “Can we…can we try this again? Maybe without the jumping at you like a crazy person part?”  
> Jeff surprises Annie at her apartment, but things don't go completely according to plan.

Everything was going great until this point. His brief crisis after landing in DC was over and done with. And after getting a drink and some motivational words from a stranger at a bar, Jeff finally grew a pair and took a cab to Annie’s place. He even bought her some flowers on the way, which were admittedly a little withered already, but it was the best he could find in a gas station at almost 9:00 in the evening. He told himself that it was the thought that really counted. 

He had contemplated changing into something else before meeting Annie but decided that his current outfit was actually perfect. His dark grey shirt and jeans combo looked nice, but not too nice. It was the sort of outfit that said _‘I did put some thought into what I’m doing here, but not to the point where I would clearly expect tonight to end in something more than platonic shoulder-holding’_ which was exactly the message he wanted to send. And he really didn’t expect anything more than that from tonight. _Maybe tomorrow…_

Silently scolding himself for even slightly opening the door to that particular chamber in his mind, he quickly shook off any non-platonic thoughts and made his way to Annie’s apartment. He was walking with intent, because he had a clear plan in his head.  
After knocking on her door, she would open it and be surprised but happy to see him. He would greet her by saying ‘mi’lady’ and she would smile, maybe even giggle a little bit before answering ‘m’lord’. Then they would hug, and she would invite him in. The hug is the part that made him a little nervous, but he would just have to focus on not taking in too much of her scent and not touch her anywhere below the shoulders and he would be fine. After that, they would talk for maybe an hour or two before he yawns, and it has to be a convincing yawn, and tells her he should probably head back to the hotel. They would set a time for when they’re going to meet tomorrow and that will be that.

That was the plan. It was a good plan. One that he would be able to pull off and that would guarantee that he was always in control of the situation. 

The only problem with that was that his plan flew straight out the window the moment Annie opened the door.

“Mi’lady”

Jeff managed to execute that first part of his plan just before the connection between his eyes and his brain started working and the picture in front of him was fully processed. At which point his brain just short-circuited and automatically deleted everything he had planned for tonight or any other thought he had that didn’t include the _not so little_ miss Edison before him.

Maybe it was the fact that he hadn’t seen her in two months, maybe it was her outfit which, consisting of only some tight fitting yoga shorts and a tank-top, was way more revealing than any of the pyjamas he remembered her wearing back in Greendale. But either way, he realized more than a few seconds too late that he was ogling her. His eyes must have wandered up and down Annie’s body at least three times before he finally regained control over them and forced himself to look her in the eyes. 

A move he regretted almost immediately, as the big blue spheres starring back at him just caused his insides to melt even further. He couldn’t accurately read her expression, but those eyes spoke a language of their own.

“Uhm…hey.” He said, giving conversation another shot, hoping to get a response from her this time.

But she didn’t say anything. Why didn’t she say anything? He had said something didn’t he? Was this already going badly? He should have just stayed at home…

He couldn’t tell if it had been seconds, minutes or hours before Annie finally broke the awkward silence between them. She did so however, by jumping at him without a warning and wrapping her arms around his neck in a tight embrace. So there’s the hug he expected. What he didn’t expect was that she literally launched herself at him.

It happened so fast that he just managed to carelessly drop the flowers to the floor before catching her in his arms. Unfortunately for him, his already buckling knees didn’t catch up to the situation quickly enough and Jeff couldn’t keep them both upright. He lost his balance and fell backwards, landing on the unforgiving ground with a hard _thud_.

“Annie! Are you trying to kill me?” He said with a slightly sharper tone than intended, as the pain spread through his back.

But with Annie lying on top of him now, that pain faded away almost instantly, as he couldn’t help but take in the scent of her shampoo, which he would put somewhere between lavender and green apples, completely unsure if it was even remotely close to either of those things, but very sure that it did things to him he would have rather liked to avoid tonight. Especially in their current position, as Annie would probably be able to feel any sort of uncontrolled movement happening _downstairs_. Similar to how he was able to feel right now that she wasn’t wearing anything underneath her top…which he definitely didn’t focus on in any way. 

His hands had meanwhile developed a mind of their own and were already way too low on Annie’s back and he caught them just in time before the situation turned even more awkward than it was already. If that was possible at all. 

_‘Well’_ he thought to himself _‘that could have gone a lot better…’_

\----

Her life almost flashed before her eyes when she realized they were falling. In the end, it was only the moments she had shared with Jeff that did appear in her mind. Because while the fall she was currently experiencing in slow motion would definitely not kill her, Annie was certain that by literally jumping at him before even saying so much as ‘hello’, she just effectively murdered any chance of their reunion being a somewhat normal affair. 

What the hell was she thinking? It all just sort of…happened. She couldn’t even comprehend all the emotions she felt when it was _him_ standing on her doorstep and so she just thought…well actually she didn’t think, she _acted_. And she was regretting that lack of thought right about now.

So, after landing on top of him, she figured that her best course of action was to not speak a word, as whatever would come out of her mouth would most likely just make things worse. Instead, she waited for Jeff to say something. It took him a while to do so. Probably due to the wind being knocked out of him by her full body weight crushing into his chest, which Annie definitely didn’t feel up for a second to check if it was still as muscular as the last time she felt it…it was. 

“Someone missed me” he said, trying to sound as calm and collected as possible. But if Annie hadn’t buried her face in his chest to hide her own embarrassment, she would have seen the red in his cheeks and the panic in his eyes.

Finally accepting that she couldn’t just stay quiet the entire time, Annie didn’t even attempt to fake confidence. 

“Can you please not look at me right now…or ever again”

She lifted her head from his chest while he lifted his up from the ground and they ended up looking each other in the eyes, sharing a moment of silent understanding before they just started laughing. At each other, at themselves and at the universe which apparently hadn’t yet run out of ways to put these two in awkward situations.

“Can we…can we try this again? Maybe without the jumping at you like a crazy person part?”

“Only one chance to make a first impression I’m afraid”

Annie rolled off him with a sigh and they both got up. She was worried for a second that Jeff might have hurt himself, since he basically took the full force of the fall and her landing on top of him. But then she remembered that the weights he lifts when working out probably weigh as much if not more than her, so he was probably fine. 

Looking down the hallway to see if any of her neighbors decided to check out the commotion happening outside their door, she was relieved to see all doors remained closed and the hallway remained silent, except for the sound of Jeff dusting off his button-up. 

It was then that she noticed the flowers scattered around on the floor. 

Feeling guilty for ruining his sweet gesture, Annie apologized to Jeff as she picked the roses up from the ground. “I’m so sorry Jeff, I totally ruined it…”

“Yeah, you really did” He replied with a grin, but he immediately rowed back when he saw that she actually felt guilty about it. “Look Annie, it’s ok. Really, it is. It was crazy to just surprise you like that”

“No, Jeff…it…it was sweet” She said, giving him a reassuring smile while picking up the last few roses. “I like surprises”

Jeff chuckled slightly before expressing his doubt about that statement. “Annie, I know for a fact that you don’t like surprises. You literally once scheduled in 90 second breaks to rest our brains during a study session”

“Well excuse me for wanting to be prepared” she replied with played indignation. “That doesn’t mean I don’t like a surprise from time to time”

“Glad I could provide you with one of those then” he mockingly said with an ironic grin “But you don’t have to immediately surprise me back next time alright?”

A silly thought popped up in her head and she almost dismissed it as such. But realizing that the last few moments were probably as weird as it gets anyway, she decided that she might as well go through with her silly little idea.

“What did you think was going to happen then? When you knocked at my door and I opened it, what was your plan?”

He took a while to comprehend the question, before shrugging his shoulders and letting his gaze wander around aimlessly. “I guess the way I envisioned this, you would have greeted me verbally instead of committing physical assault. And those flowers would have found their way from my hands to yours without either me, you or them landing on the floor”

Her lips started to form a smirk, and Ignoring Jeff’s questioning look, she held the flowers against his chest, motioning him to take them from her. 

“Annie...” he said with his eyebrows still raised in surprise. “you do realize that I bought these for you right? Because I’m not the kind of guy who just buys flowers for himself for fun”

Rolling her eyes, she thrust the roses into his chest, practically forcing him to take them. “Trust me ok?”

And he did. So he took the roses back, still with no idea what Annie was planning. And his surprise was even greater when she just disappeared into her apartment again, looking over her shoulder and flashing him a coy grin before closing the door behind her.

Considering for a second to just let him stand there for a while, but deciding that he would probably be confused enough as it is, she told him what to do while barely managing to contain her laughter

“Knock again!” 

And sure enough, Jeff did as he was told, and Annie opened the door for him for the second time that night. 

She leaned against the doorframe with one hand and put the other on her hip trying to look as confident as possible the second time around. With a wide smile and a shine in her eyes she greeted him properly and without any danger of physical injury this time. 

“M’lord…”

The moment lasted for a second, before they both broke out into laughter. Still not perfect, but definitely better than the first time. 

She was sure that they must have annoyed at least some of her neighbors by now, so she quickly invited him in and closed the door behind them. 

“I’ll get something to put these in” she said, taking the roses and nodding her head in the direction of the little couch she had in her living room area. “make yourself comfortable, I’ll be right back”

He gladly took her up on the offer and sat down on the sofa which he distinctly remembered seeing in an IKEA commercial not too long ago.

Annie didn’t let him wait for long and soon returned with the roses now neatly bundled in a pitcher.

“I didn’t have an actual vase to put them in, but they look nice like this too don’t you think?”

He nodded in agreement as she put the flowers down on the small coffee-table before them. 

“I’m glad you like them” 

She gave him a warm smile as if to ensure him that she actually did like them, before sitting down on the couch beside him. They weren’t touching, but the piece of furniture was so small that there really wasn’t any way to avoid that if one of them only moved an inch. 

And it didn’t take very long for that to happen, as she turned towards him, brushing his leg with her knee in the process. It was the slightest of contacts, but they both felt it nonetheless. 

“So, what brings you here?” She asked, getting the obvious question out of the way.  
Jeff knew of course that he would have to answer that one pretty early on, but he still didn’t have a real response at the ready.

“Well…I mean I’m here because of you obviously”

Annie’s answer was a comforting smile, showing appreciation for his words, but also clearly not accepting that as his full answer. 

So he continued, not entirely sure where he would go with his explanation.

“I guess I just wanted to check in you…see how you’re doing and…you know”

Her smile didn’t fade away completely, but it wasn’t as wide as it was a second ago. 

“Really? And you’ve planned this for how long?”

He again took a little more time than he should have to answer. 

“Probably…let me think…” In the middle of fabricating his fake process of planning a trip to DC, he made the mistake of looking at Annie again “oh who am I kidding, I can’t lie to you when you look at me like that”

Her smile grew wider again in triumph, but she made sure to continue looking at Jeff expectantly, as she was still waiting for a real explanation.

“Look Annie, I didn’t plan this at all ok? It was a spur of the moment decision, Britta called me yesterday and told me she had booked a flight to DC but couldn’t take it because she…well she explained it the next day but it’s really not important and I only got half of it anyway. What matters is that one thing led to another and now I’m sitting here in your apartment”

After finishing his surprisingly unspectacular story, he didn’t even dare look at her. He just hoped that she would be satisfied with what little he had offered her. Because there really wasn’t a lot more to tell her about the factual events that led up to where they were now. Any further explanation would include those damn emotions he begrudgingly developed over the last few years, and he really didn’t want to get into those right now.

But luckily for him, Annie didn’t try to dig any deeper, instead focusing on what he had revealed to her thus far.

“I should have known Britta was involved” 

“She always is” He replied with annoyance in his voice that was maybe only half-faked.

“You would know” She said, adopting a more mocking tone along with a smug grin appearing on her face. “I mean, you almost married her like what? Three times already?”

“That’s not-“ She didn’t let him finish his retort before shoving him harshly, almost causing him to fall off the couch. 

“Is that what this is about? Are you two engaged again!?”

Not completely certain whether she was being serious right now, he made his best ‘outraged’ face and gave her a little shove back. 

“No! Of course not! Why would you even think that was a possibility?”

She shrugged and tilted her head slightly, as if to get a different angle on Jeff, that would somehow reveal more about his thoughts.

“I don’t know, I just figured you probably hooked up at least once or twice since I left”

Jeff almost jumped up at that remark. Was she really thinking that? And did she put more emphasis on the last part of that sentence, or was he just imagining things?

“Annie I….no, just no. We did not. Britta and I are past that, we’ve been past that for quite a while” 

He could only hope that the impression he gave her didn’t bring across the question he had in his mind, _‘I don’t know if you and I are past that though’_

He dismissed the thought as quickly as it came, blaming it on his lack of sleep catching up to him.

“Are you happy about it?” Annie asked innocently, trying hard to not combine her question with any implications.

“About me and Britta?” Jeff asked back, in part to clarify but also in part to buy time.

She nodded in response.

Jeff let his eyes wander around the room for a moment, trying desperately to find anything to focus on that wasn’t a part of Annie.

“I think so. Yes, I am. And she is too, if that’s what you’re asking”

She gave him an unsure smile, not totally convinced that it was the appropriate reaction to his words. Her subconscious had already formulated the logical next question for her, _‘and what about us? Are you happy with the way we are as well?’_ but she wasn’t yet tired or desperate enough to actually ask that question out loud. And looking at Jeff, she could see that he seemed to have a similar problem.

So they sat in silence for a while, occasionally looking at each other and smiling shily before turning away again whenever their eyes met. 

It must have been almost a minute before Jeff finally went onto another conversation topic. 

“Your place is nice, much better than the old one”

“Thanks!” She replied, visibly relieved at the change of topic. “It’s nice to finally live in a ‘grown up’ apartment for once”

Amused at her choice of words, he picked up a pillow from the seat next to him and held it up like it was a piece of evidence in a court case.

“You still got rainbow colored pillows lying everywhere”

Rolling her eyes at him, she snatched the pillow from his hand and held it close to her chest.

“I just happen to be a grown-up who likes pink fluffy pillows! There’s nothing wrong with that!”

He chuckled at her immediate desire to defend herself and leaned back further into the couch.

“Guess not, but I bet if I walk over into your bedroom right now, I would find not only pink fluffy pillows, but also at least five stuffed animals lying on your bed” 

Blushing more intensely now, Annie couldn’t think of a reply that wouldn’t give away in one way or the other that he was pretty much spot on with his assumption.

And her hesitation didn’t go unnoticed.

“I’ll take that as a ‘yes’” Now it was Jeff’s turn to put on a triumphant smile.

Not willing to give up so easily though, Annie decided to counterattack instead.

“Well, I’m sorry that not all apartments can be as boring as yours! I mean, would it kill you to just put in a dash of color somewhere?”

Clearly unhappy at the critique of his interior design skills, he replied with a little more edge in his tone than necessary.

“That’s so not the point of interior design Annie! My apartment has a consistent theme ok?”

Annie sensed that she was slowly gaining the upper hand again.

“Jeff, your apartment looks like a commercial. You’re supposed to _look_ at those designer catalogues, not actually _live_ in them. You have to give your place some character as well!”

He thought about his next argument way more than he should have, this was a competition now.

“I don’t think having stuffed animals in my bedroom counts as ‘giving the place character’”

She had to admit that that stung a little, but it wasn’t enough to derail her concentration. She was in debate mode now and this discussion became a lot more important than it had any right to be.

“The fact that you’re focusing on my stuffies again just shows how weak your arguments are” And if she was in a real debate, she probably would have left it there, but with her personal pride being at stake, she foolishly gave him another opening. “And who says that I didn’t just leave them in Greendale when I moved here?”

Jeff recognized his opportunity and seized it without hesitation.

“Well, why don’t we take a look into your bedroom and find out”

Just five minutes ago, he would have kept a sentence like that in his head and the clear implication that came with him wanting to get into her bedroom would have prevented him from saying anything like that out loud.

But now, he noticed that implication just a second too late and he could only hope that he got lucky and Annie didn’t pick up on it at all.

Unfortunately, judging by her sudden change in expression and the seconds of awkward silence that followed, he figured that his luck must have run out some time ago.

And so it was half about their argument on interior design, and half about the unintentional innuendo when she finally answered.

“Jeff, I will not show you my bedroom” She tried to balance irony with firmness in her voice but wasn’t entirely satisfied with either side of it. 

Jeff wasn’t sure where to go from here. He could probably just make a joke and get this conversation somewhere more comfortable. But he also felt like that would just be admitting defeat. Not against Annie, but against the idea that he could never have a normal conversation with her again. He couldn’t just do a 180 and turn back every time they so much as touched more risky areas. He thought to himself that there shouldn’t be so many boundaries when talking to a friend, especially one as close as Annie was to him. 

“How about I take you out to dinner first then?”

Annie’s expression changed rapidly again. She visibly lightened up and nodded at him.

“I’d like that. Tomorrow?”

Jeff was relieved to hear a change in tone as well. Maybe this would go according to plan after all. 

“Sounds great, you know a place?”

Thinking about it for a second, Annie excitedly told him about a new Burger place she had found that they could reach on foot from her place.

Not happy with the amount of carbs he would have to consume, Jeff needed some convincing, but ultimately gave in surprisingly easy and they set the date for the next day.

They continued their conversation for a while after that. He told her about his flight and his arrival in DC. And it didn’t take her long to go into full planning mode, making a list of all the sights she wanted to show him during his stay. But it became pretty clear after little more than an hour, that neither of them had slept a second the night before, and that they wouldn’t be able to stay awake much longer with most of their conversation being interrupted by occasional yawns which became more and more frequent as time went on.

In the end, it was Annie actually dozing off for a minute that got Jeff to call a cab and prepare for going back to the hotel. A few minutes after that, they got up from the couch and she walked him out.

It wasn’t until they were at her door and she looked up at him with some sort of expectation in her eyes that it dawned on him that he would have to hug her goodbye. The painful memory of their last hug still fresh in his mind, he tried to do everything right this time, but they somehow ended up clashing arms and not finding the right angle several times. It brought up flashbacks from their first year at Greendale, after they had beaten city college in the debate. And he seriously considered for a second to just pat her on the head like he did back then. 

But fortunately for him, Annie wasn’t going to let that happen and instead took a step towards him. She leaned up to give him a little kiss on the cheek, before wrapping her arms around him and squeezing him tightly.

He was dumbfounded for a moment, but quickly returned the embrace, endlessly thankful that at least one of them hadn’t lost their capability for basic human interaction.

If they’re friends had been there with them, they probably would have commented on how long that hug went on. But they were alone, so neither of them cared. Jeff was actually a little disappointed when Annie let go of him, but he was instantly compensated when he saw her wide smile and shining eyes looking at him. 

“Good night Jeff” She said and batted her eyes at him, not even starting to comprehend all the things happening inside him after she gave him that slightest of gestures.

He silently accepted right then that he was done for. It actually took a lot more of his restraint than he was comfortable admitting to not grab her right there and pull her into a passionate kiss followed by who knows what. And the way she was looking at him, he wasn’t even sure if that’s not exactly what she wanted him to do.

But his restraint won out tonight. And he returned her “Goodnight” with a smile before turning away and heading down the corridor. He didn’t dare turn around again until he heard her door close behind him, causing him to let out a sigh of relief. 

He really couldn’t tell for sure if he would have been able to resist his most basic longings for Annie much longer. And the mere thought of what could have happened if he had acted on them accompanied him into the cab and all the way to his hotel room.  
He fell asleep that night, knowing that he would dream of her. And that he would wake up the next day with the bitter realization that his dreams hadn’t magically come true overnight.

But even more importantly, his last thought before drifting off, after having been deprived of sleep for far too long, was that he had to figure out where they would go from here. Because what ever that feeling was that he felt when he saw her tonight, it sure as hell wasn’t something he could ignore much longer.

**Notes for the Chapter:**

> Thanks for coming this far!
> 
> I didn't originally intent for this chapter to only include the scene in Annie's apartment, but that part just got longer and longer as I was writing it and so I decided to just dedicate the entire chapter to their chaotic first interaction. I think the next chapter will be a lot more about actual plot progression, otherwise I'll never get anywhere with this. But who knows, maybe I'll get derailed again...
> 
> The next chapter will probably come out over the weekend, maybe early next week.
> 
> Any comments and feedback are greatly appreciated!


	4. To date or not to date

**Summary for the Chapter:**

> "you told me that over all the years you’ve known Jeff, and even now after you came here to DC, you just wanted him to finally make a move"

**Notes for the Chapter:**

> I tried a lot of different things with this chapter and it kind of got out of hand, which is why it is a lot longer than the previous ones. Hope you'll still enjoy it!

Annie woke up the next day to the sound of her alarm. She felt more tired than usual, trying to remember what caused her to get so little sleep last night. Rubbing the sleep from her eyes, she tried to turn on her nightstand-lamp and found the switch on her second attempt. She sat up and stretched her arms wide, before stifling a yawn and forcing herself to get out of bed. The lack of sleep over the last few days was starting to get to her, but she was determined not to let that be an excuse for being late to work. Although late in her case meant being anything less than half an hour early.

Walking into her living room, she was a little surprised to see some flowers standing on her coffee table. But it didn’t take long for her brain to reconnect the dots and the image of Jeff surprising her last night with a bunch of roses reentered her mind. The thought of him brought a smile to her lips and the lack of sleep instantly felt like much less of a burden.

Much more contempt with herself, as her sleepiness gradually made way for the memories from last night to return, she practically floated into the bathroom and took her pyjamas off to take a quick a shower. The warm water further reawakened her senses and she felt much more energized when she got out of the cabin and wrapped herself in a towel, before walking back into her bedroom to put on some clothes. 

Slightly annoyed at herself for not picking out an outfit the night before, Annie quickly put on a plain white bra and matching panties under a knee-length black skirt and a blue blouse. It was a combination she knew worked well, but she still checked herself in the mirror to make sure her outfit was presentable.  
She made her way to the kitchen and put on a pot of coffee, before opening her cabinet and picking out her favorite cereal. She considered for a second to make herself some pancakes but decided that the extra sugary brand of cornflakes would be enough of a treat for now. She put the cereal in a large bowl and went to grab a milk carton out of the fridge, when she noticed the little post-it note that she had put up on the refrigerator-door. It was the one her father had given her two nights ago.

At first, she wanted to throw it away immediately, since she had no actual intention of calling the number written on it. But she somehow couldn’t get herself to go through with it. There was always that small part of her that thought there was still hope for her dad. That there was still hope for a healthy relationship with him and that she should just call him and talk things out. And however small that part might be, it prevented her from throwing away this one connection she had to her father.

So she did her best to ignore the note, as she grabbed the milk from the refrigerator and prepared her breakfast. 

While she was eating her cereal and drinking her desperately needed cup of coffee, she couldn’t help but think of Jeff again. There was no denying that she was more than a little bit excited about seeing him again after work tonight. Him showing up at her apartment only a day after the not so welcome surprise of meeting her father there must have been some kind of divine intervention, because it was exactly what she had needed at that moment. 

She needed to be reminded that her real family, the one she chose when she enrolled in Greendale, would always be there to pick her up when she was down. And that they would never abandon her the way her past family did.

The thought stuck with her after she had finished her breakfast and prepared for work. Because maybe that’s what going out with Jeff tonight was all about. Sure, she would have a great time and she was really looking forward to it. But in a way, it was also an active decision for her Greendale family over the one that had let her down over all those years. She actively chose to spent time with Jeff and denied her father the opportunity to even speak to her over the phone.  
Because Shirley was right, she thought to herself as she glanced one last look at the note on her fridge before leaving her apartment and heading for work. She really didn’t owe her dad a thing, not even a phone call.

\---

The sun was already blinding him through the window when Jeff woke up. After a short period of disorientation and confusion due to not waking up in the familiar environment of his apartment, he clutched his hands over his face as the memory from last night kicked in. He had been to Annie’s place. He had seen her, hugged her, talked to her and he distinctly remembered feeling her lips on his right cheek. That actually happened.

He brought his fingers to the spot where she had kissed him, and the emotions from last night washed over him again in full force for just a second. It was a moment of happiness for Jeff that was crushed immediately by the all so familiar feeling of guilt returning quickly. _‘what the hell was I thinking? I was supposed to let her go!’_ he thought to himself while rubbing circles on his temple as if that could turn back the clock.

Accepting the failure of that attempt, he reached over to the nightstand to check his phone, but it wasn’t there. After panicking for a second, thinking he might have left it at Annie’s place, he remembered lazily taking his shirt and pants off in the bathroom before preparing for bed last night. His phone was probably still in his pocket.

So he got up from bed but instantly felt the soreness in his back, which he could only accredit to the awkward fall he had yesterday, when Annie made it a little _too_ clear how excited she was to see him.

Doing his best to ignore the aching pain, he went over to the bathroom and found his clothes from last night neatly folded beside the sink. He couldn’t accurately remember putting them there, but he knew from experience that his tired self was capable of quite a lot. 

As expected, he found his phone in the back pocket of his pants and quickly unlocked it to check the time and read any incoming messages. It was 9:00 am. And there was one message. It was from Annie. 

His mind went into overdrive the second he processed that information. In his head, there were already hundreds of possible scenarios concerning the contents of that text message. Most of them included some form of heartbreak. 

He stared at his phone screen for at least a minute, contemplating his next move. He didn’t really see a way to make not opening the message somehow acceptable. Annie knew he was on his phone all the time. She knew there was no way he didn’t see the message. And thus, not reading it would most likely be the worst option of all. 

After coming to that conclusion, Jeff stopped delaying the inevitable and opened the message, bracing himself for the worst.  
\- _Was great to see you last night! Hope you’re having a great day and I’m really looking forward to later <3 _

_‘Well, that could have been worse’_ Jeff thought to himself _‘That was…short. And sweet’_ And it wasn’t a big deal, which Jeff had a hard time understanding. He was used to Annie making him feel such a great array of emotions that sometimes made him non-ironically worried for his mental and physical health. But this little message was none of that. It just sort of gave him a warm feeling in his stomach and made the corners of his mouth curl up slightly. He had expected to be hit by a storm, but instead it was just a gentle breeze, slightly tingling his senses. 

To Jeff it was perfect. It gave him a new perspective, one through which this whole Annie-thing didn’t seem like that big of a deal after all. It was the first time that he allowed himself to think of it as just a casual thing happening between two friends and they could just see where it goes from there. Until now, he could only see two ways his relationship with Annie would go, it would either end in heartbreak after losing her for good this time, or it would end in him being a burden to her career and her development as a person. And while he did not yet fully accept the possibility, in his mind he slowly started to open up to the idea, that there might be more than these two possible outcomes.

He quickly wrote a text back and hit send.

\- _I really enjoyed yesterday too. My back is still a little sore though… Can’t wait to see you again tonight! ;)_

He thought about sending her a heart back but figured that it would probably seem a little weird coming from him. And before he could dwell on it any longer, his stomach made itself known with a loud grumble. A stark reminder that he hadn’t eaten anything since his plane ride, apart from a little salad he bought and ate at the hotel while waiting for his room to be cleaned. Checking the time again, he figured that if he hurried up a little, he could probably still make it to the hotel’s breakfast buffet before it closed, so he wouldn’t even have to leave the building or pay extra to get something to eat.

Determined to get his metabolism back on track, he quickly took a shower and put on some casual clothes, a pair of jeans and a black t-shirt, before taking care of his hair and doing the most basic skin-care routine he could lower himself to without developing intense hatred for the image he saw in the mirror.

After deciding that his look was at least acceptable, Jeff wasted no time and grabbed his key card as he left his hotel room and headed towards the elevators. He pushed the little button with the arrow pointing downward and pulled out his phone while waiting for the elevator to arrive. About 20 seconds later, a loud _ding_ sound announced that it did, and the doors opened, allowing him to enter the cabin. There was one other person in there, also on his way down, and Jeff gave the man a brief smile before looking back at his phone. And while he didn’t recognize him at first, the sound of his voice quickly reminded Jeff that he actually knew the person standing next to him. 

“Jeff! You’re staying here too?”

Surprised at hearing the man say his name, Jeff turned towards him again in confusion, before recognition finally hit him.

“David! I’m sorry, I didn’t even recognize you at first” he said with a dumbfounded look on his face. He hadn’t really expected to meet David again. And definitely not so soon, or in his hotel on the way to breakfast.

“Took me a second too. You’re on your way to the lobby?” the older man said while pointing at the control panel.

Jeff shook his head. “Actually, I’m on my way to the restaurant, was hoping to catch the breakfast buffet before they close today”

“Oh really?” David replied in a surprised tone. “I took you for one of those ‘get up at 6:00 am and start the day with a 5 mile run’ kind of people. Surprised to see you eat breakfast at 9:30”

Jeff chuckled at the remark. “5 miles are only on Wednesdays, and whoever said you have to wake up early to stay in shape was a liar. Besides, I went to bed a little later than expected last night”

Clearly reading into his words, David smiled at him knowingly and said “So I guess that non-date with your friend went well then…”

Jeff tried to remember exactly how much he had revealed to David when they had talked at the bar the day before. It must have been a little more than he would have liked to. 

“you could say so” He explained vaguely before stirring the conversation into a different direction. “So, you’re on your way to breakfast too?”

“I am, actually” David said as he looked at his watch. “It’s later than usual, but we’re two hours ahead from where I live, so I guess that’s to be expected”  
There was another _ding_ and the elevator doors opened. They got out and made their way to the restaurant area where they found a lot of free tables, as most other guests had probably already finished their breakfast.

David pointed at a table by the window-front and Jeff nodded in response before they split off into different directions. Jeff went over to a little stall in the corner of the room, where a chef was taking orders for fresh omelets and scrambled eggs. He ordered an egg-white only omelet and made his way to another table where a steaming coffee pot was waiting for him. He poured himself a cup before returning to the food-stall and grabbing his eggs. 

He went over to the table that David had pointed out earlier and it didn’t take his new friend long to join him there with a plate of bacon and fried eggs and a coffee cup of his own. 

“Just egg-whites huh? My doctor told me to try that, but I could never really be bothered”

Jeff had endured comments like that for far too long to actually be provoked by them anymore. His retort was well rehearsed by now.

“There are certain prices you must pay, when you want to look like me” He said while putting another forkful of egg-whites in his mouth.

David laughed at his words and pointedly took a bite out of a strip of bacon.

“Well, I didn’t look like you even in my thirties so why bother now right?”

They talked a little more about Jeff’s dietary choices and how David should probably start implementing some of them in his own diet if he wanted to see the other side of 80, before they went on to a few other topics and ended up spending over an hour at their table. They were on their third cup of coffee each when David brought up one particular topic again.

“So, you’re going to see your _friend_ again soon?”

The way David emphasized the word friend didn’t go past him, but Jeff decided not to focus on that right now.

“Actually, I’m meeting her again tonight, we’re going out for dinner”

David smiled slightly before taking a sip of his coffee. 

“You know…” he said as he put down his cup. “I think you’ll end up having an actual date if you’re not careful” 

“I don’t think I’ll be in any danger of that happening” Jeff said with a mocking tone, hiding the fact that he was actually worried a lot about that very thing. 

David reacted with exaggerated confusion “Did something happen in the last 20 years that I just wasn’t informed about? Is having a date a bad thing now? I’m genuinely confused”

Jeff thought about what to say next. It really wasn’t easy to explain the situation to someone who hadn’t witnessed all the history between Annie and him. It would be hard enough to explain it to one of their friends. 

“It’s not about having a date in general. It’s about who you’re having that date with. Things are…complicated between us”

Clearly not satisfied with that explanation, David quickly asked a follow up. “The good kind or the bad kind?”

Jeff was confused by the question. “There is a good kind of complicated?”

“Damn right there is” David replied without hesitation. “It’s the kind of complicated that just sorts itself out after you get your act together!” 

There was a time when he would have gladly accepted such a logic, Jeff thought to himself. There was a time, when he was so convinced that he could solve basically any problem with ease, and that if he got his act together, he might just be able to do even impossible tasks. But that past version of himself was long gone. And his current self wasn’t as confident in his own abilities and this version cared way too much about Annie to jeopardize everything with such naivety.

“It’s not that easy. There is a lot of…history. Sometimes people just…aren’t supposed to be together”

David shook his head, he almost seemed frustrated.

“Well what is that supposed to mean? Who gets to decide if you’re supposed to be together? You like her, don’t you?”

“Well yeah but-“

“And you want to make her happy?”

“Of course, it’s just-“

“Then that’s all you have to worry about. That’s your part of the decision. She will take care of her part, and if it works out then it will and if it doesn’t work out than it won’t. Simple as that”

Before Jeff could reply, they were interrupted by the sound of David’s phone ringing. He didn’t hesitate for a second and picked it up, his expression lighting up in the blink of an eye. 

“Hello?” 

And as quick as his expression had light up into a bright smile, it soured again. Jeff could only imagine that whatever David had heard when he answered his phone must have disappointed him greatly. 

“Everything alright?” He asked after David had hung up.

“Hmm? Oh, yes, it’s alright”

It wasn’t hard for Jeff to see that he was lying. 

“Bad news?” He asked, trying to read the expression in the older man’s face.

“No, nothing like that” David said, struggling to find the right words. “It’s just...I’m waiting for a certain someone to call me”

Jeff nodded understandingly.

“And I’m assuming that wasn’t that someone?”

“No, it wasn’t”

\---  
“Annie, are you ok?”

Annie snapped out of her daydream and was slightly disoriented at first. She looked around to see who was talking to her before finding her coworker sitting next to her. 

“Uhm...yeah Sarah, I’m alright. Why?”

“Well” Sarah said with a somewhat concerned look “you’ve been acting weird all day. You were later than usual, and you seem distracted somehow. Also, we’ve been sitting here for five minutes and you haven’t even touched your lunch yet”

Annie looked at the food in front of her, not feeling any appetite.

“I’m fine, I’m just...a little nervous I guess”

Sarah pulled her eyebrows together in confusion.

“Nervous? Annie, what are you nervous about? Is your evaluation up today?”

“What? No, that’s not for another two weeks” Annie said, before realizing that that would have been a good opportunity to distract from what actually had her distracted all day. 

“What is it then?”

Annie tried to come up with a lie to tell her coworker, but she ultimately decided that there was no real harm in telling Sarah about her plans for the evening.

“I’m just meeting somebody tonight”

Sarah’s mouth opened in exaggerated shock. 

“Oh my god. Annie’s going on a daaaattee”  
Annie couldn’t even get a response out before her coworker had already scooped over closer to her and wrapped her arm around her, squeezing her tightly. 

“Tell me everything!”

A slight blush crept up Annie’s cheeks. She had tried her best to not think of her dinner with Jeff tonight as a date, but she couldn’t deny that the idea was more than a little tempting. 

“Well, his name is Jeff, and-“

She was interrupted by Sarah suddenly grabbing her arm and looking into her eyes intensely. 

“Jeff? THE Jeff? The one you told me about in the bar the other night?”

Annie’s eyes went wide. She didn’t even remember telling any of her coworkers about Jeff. But the night that Sarah was referring to was sort of a blur in her memory. It was her first night out with her new friends in DC. She had been there for about a month at that point and she figured that it was a really good opportunity to socialize. And she may have had one or two or ten drinks too much and ended up on Sarah’s Couch the next morning. She felt bad about it for a while, but it was a fun night, and there weren’t really any meaningful consequences. Until now.

“Maybe...what...what did I tell you about him”

Sarah smiled at her concern, and playfully rubbed her chin to indicate that she was trying to remember Annie’s words.

“Oh, not that much. Only that he’s a guy you met in college. You said he was a little older but very handsome. And I think you said you were good friends”

Annie let out a sigh of relief. While it might have been a little embarrassing, it wasn’t a big deal that she met and befriended a handsome guy in college.

“Yeah, there isn’t much else to say really”

“Oh wait, you actually told me a little more than that”

The alarm bells in her head started again. She knew that there were a lot of thoughts and feelings about Jeff stowed away inside her. And she desperately hoped that the alcohol hadn’t been brought them to the surface that night.

“What-“

“You told me that he has a great body, and that you could spend days just staring at his abs”

“Oh my god Sarah-“

“And you had a crush on him for years. And that you pretended to be his wife at one point”

“Sarah please-“

“I think you also said something about dancing for him in a Santa costume, and you definitely said something about kissing him like three times and how those were the most fulfilling moments of your life”

“Sarah, I’m leaving now” Annie said and got up from her seat. It was bad enough to have these thoughts inside her head, there was no need to have them thrown at her from the outside as well.

But Sarah grabbed her arm again and looked up at her with an apologetic expression. Annie quickly turned her face away to hide the intense blush she felt on her cheeks, that had reddened more and more with every word she heard.

“Oh come on, it’s no big deal!” Sarah said, trying to convince Annie to stay. “We’re friends, right? And besides, I haven’t even told you the most important thing”

Annie really didn’t want to hear any more of her drunk confessions about Jeff, but she sat down nonetheless, mostly because she felt like she needed to know what Sarah knew, to avoid any further embarrassments in the future.

“Ok...what would that be?”

Happy that Annie was staying, Sarah smiled and playfully cleared her throat as if she was about to make a big announcement.

“That Night when you were totally out of it and pouring your heart out, you told me that over all the years you’ve known Jeff, and even now after you came to DC, you just wanted him to finally make a move. And it seems to me like he did. Better late than never huh?”

\---

The conversation was stuck in her head for the rest of the day. And while the initial embarrassment wore off over the course of her shift, to the point where she stopped considering changing her name and moving to a different state, she still thought a lot about what Sarah had said. 

It wasn’t that she didn’t trust Sarah or was afraid that the information would make its way to someone who could do harm with it. But in a weird way, Annie felt that the fact that someone else knew about those deep and secret thoughts of her meant that she could no longer deny them. They were no longer a pure product of her imagination. She had put them out there and they were real now. 

And as she sat in the bus on her way home, going over that conversation in her mind again, she remembered one part of it especially. Sarah had called her meeting with Jeff tonight a date. And more importantly, Annie didn’t feel the need to immediately correct her. It wasn’t something she did on purpose or with any real thought behind it, but it still happened nonetheless. Someone suggested that she was going on a date with Jeff, and she didn’t deny it. Which in this case was basically equal to just confirming it. And it wasn’t until she left work that she fully comprehended the implications of that. She was going on a date with Jeff Winger. Or was she? It’s not like they really called it a date, and Annie was sure that if they had done that, Jeff would have just gotten scared and run away. So it probably wasn’t a date. Or was it? 

The thought didn’t leave her until she got home and opened her apartment door. But looking at her watch she realized that she would have to hold that question for later, because she only had about an hour before Jeff would arrive. 

She used that time to freshen up in the bathroom and took a look in her closet. She hadn’t yet picked out an outfit for tonight, but she definitely thought about it at work and on her way home. It was a warm day, and she figured that it would make sense to put on one of her summer-dresses, although the fact that she knew how Jeff had always enjoyed to see her in them might have played a role in the decision as well. After going through her entire collection twice, she finally picked out a dark green dress, with a discreet slightly darker shaded floral print. 

She hadn’t worn that particular dress in a while and was worried that it might be a bit short. She wasn’t sure about where this evening would go anyway, so the last thing she needed was to send some unintended messages with the way she dressed. But when she put it on and checked herself in the mirror, she was relieved to see that the skirt stopped just above her knees and while it revealed some cleavage, it could definitely still be considered a modest choice. 

She grabbed a thin grey sweater to go along with it before heading over to the bathroom and doing her hair. She tried a few different ways, but in the end she decided to just leave her hair open and she couldn’t help but think of that one time when she let her hair down in the study room and Jeff looked at her as if she had suddenly become a completely different, much more attractive person.

He was definitely attracted to her. Annie was sure about that. And to be honest, Jeff hadn’t really done a good job hiding it in the past. So maybe he wanted tonight to be a date too? Or did he? Determined to not let the uncertainty get to her, she leaned towards the mirror and gave herself a stern look.

“Listen Annie” she said to her reflection.

“There is only one way to find out what he wants. You will be brave. You will be formidable. And you will ask him if-“

Her psyching-up session was interrupted by a knock on the door that made Annie jump up a little. Sending out a silent prayer that Jeff hadn’t heard her from outside the apartment, Annie checked herself in the mirror one more time before she made her way over to the door.

\---

Jeff took a deep breath before knocking on Annie’s door. He was a little early, something that he was surely not particularly known for. But when it came to Annie, being punctual was just one of the extra bits of effort he was willing to make. 

And he was about to be rewarded for that extra effort, because when Annie opened the door, he was stunned into silence for the second time in a row. Last time it was because of how revealing her pyjamas had been, this time, she just looked stunning.

The simple green dress suited her in ways that Jeff couldn’t properly articulate if he tried. In fact, as soon as he saw her, he could barely articulate any proper sentence at all.

“Uhm…hey” he awkwardly mumbled, fully aware of how stupid he looked, but unable to do anything about it.

Willing to compensate for his temporary social incompetence, Annie showed him a sympathetic look.

“Hey yourself, you look good Jeff!”

“Thanks!” Jeff blurted out before his senses finally returned to him. “I mean, you don’t look too bad yourself…scratch that, you look great…that dress, it really works”

Thoroughly unconvinced by his own words, Jeff was glad that Annie didn’t seem to mind his current ineptitude and instead flashed him another smile.

“Thanks, I’m glad you like it! I’ll just grab my purse and we’re ready to go” She said as she turned around to grab the little handbag from her kitchen counter.

“Great, can’t wait” Jeff replied, trying desperately to not let her on to the fact that he just checked out her backside when she turned around. _‘Oh Annie’_ he thought to himself _‘you’re getting dangerous’_

Jeff managed to control himself a little better after that. As they made their way out of Annie’s apartment complex and headed towards the restaurant that she had picked out, Jeff was actually forming cohesive sentences again and his eyes only slipped a look at Annie’s figure like once or twice more and only when he was absolutely sure that she wouldn’t notice. 

They casually talked about how their days had been, and what they could do over the week. And it didn’t take long for both of them to leave the initial awkwardness behind and feel completely comfortable in each other’s presence again. But Annie was still determined to keep the promise she had made to herself in the mirror. So as soon as she had the feeling that their conversation was stable enough for her to bring up a heavier topic again, she finally asked the all-important question.

“Jeff, is this a date?”

Jeff’s expression gradually turned from surprised to dumbfounded as he tried to come up with an answer.

“I think…well…I mean…”

Deer in headlights was probably an understatement when it came to the way Jeff was reacting to the question. And while Annie usually felt a sense of pride whenever she could make Jeff Winger struggle for words, this time she really would have liked him to just work some of his Winger-charm and come up with a satisfying answer. 

“Jeff, don’t worry okay?” She ensured him, hoping that it would help to get out some clear words “You did nothing wrong if that’s what you’re worrying about. I just…I just want to know what this is”

Jeff nodded, indicating that he understood and respected Annie’s request, but he still struggled to come up with a real response.

“I’m sorry Annie, I know I should be able to answer that question, but honestly…I can’t really do that right now. I mean, on one hand I’m taking this really attractive girl out to dinner and I would be crazy not to label it a date the second I get the chance to do so”

His comment made Annie blush and she was thinking about how to react, but Jeff already continued his explanation.

“But on the other hand, I think about how Britta, Abed or Shirley would react if I told them that I went on a date with you. They would probably have a lot of things to say about that, definitely not all of them nice and definitely at least some of them delivered in the form of a swift right hook to the jaw”

“Ooh, you mean like that one time when I hit you in the face and almost broke your nose?” Annie chimed in, with way too much cheer in her voice.

Jeff can’t hold back a slight chuckle at Annie’s eagerness to remind him of that painful experience.

“Exactly like that, so you might see how it’s difficult for me to put a label on this” He said and pointed between the two of them.

Annie understood his struggle, she really did, but she also needed at least some clarity going forward, which is why she didn’t drop the issue just yet.

“Jeff, I know that it’s difficult, but we have to figure it out at some point don’t you think?”

He let out a sigh and looked at the ground in defeat. It was clear that he didn’t feel very comfortable talking about this, but Annie knew that they would regret it if they just avoided the issue altogether. And that she would regret giving him the option to just run away again, as he had done so many times before. 

“Look Annie…you’re right, we can’t just ignore this. But maybe we don’t need to make a decision on it right now either” He lifted his head to look at her eyes again, before going on “I know it sounds like a cop out, but maybe we should just…figure it out along the way. You know, let’s just go to dinner, let’s have a nice evening. Let’s not think about whether this is a date or not, we can just have a good time and we’ll see where it goes from there”

Annie crossed her arms before her chest and gave Jeff a skeptical look. 

“I don’t know…do you really think that’s a good idea?”

To her surprise, Jeff started laughing before answering her question.

“God no, I think it’s a terrible idea. But you know what Annie?” He put his hands on her shoulders and gave her a comforting smile. “I’ve had a lot of terrible ideas in my life. And I’ve acted on them far too often. But all of those terrible ideas and mistakes have led me up to where I am now. Standing here, in front of you, and about to have dinner with the most amazing person I know. So, who knows, maybe this is just another terrible idea that will lead to something great later on”

Annie tried and failed to find the right words for a response. She knew that he was talking his way out making a commitment. He always does. And worst of all, it always works. But she wasn’t just going to let him off the hook completely.

“You can’t just Winger-speech your way out of everything Jeff…” she said with a slightly annoyed tone. But her resentment fully fell away when Jeff put on his sweetest smile and looked deep into her eyes.

“I know” he said calmly “but…can I hug my way out of it?”

Annie rolled her eyes and swatted at his chest lightly before she wrapped her arms around him in a tight embrace.

“Maybe…but just this one time. And only temporarily, I still want an answer by the end of the night”

She really tried to sound commanding, but their current position and the fact that she was literally talking into his chest kind of diminished the formidableness of her tone.  
“Alright Miss Edison” He said before leaning down and putting a soft kiss on the top of her head.

Annie didn’t get the answer she was looking for. At least not yet. But it didn’t even bother her at this point. Because she knew Jeff was right. All of the great moments she had shared with him. All those treasured memories, they all happened as a result of terrible ideas. They were all preceded by mistakes, slip ups, complete disasters or even real tragedies. And if this night was going to be another of those memories, then she really didn’t care if it was a date, a non-date or anything in between. 

All Annie cared about at that moment was how close Jeff was to her, and how close she was to him.

And when they let go, she got all the confirmation she ever needed. Because before she could even properly process that they weren’t hugging anymore, Jeff gave her a smile that made her knees buckle a little and offered her an arm.

“Mi’lady”

**Notes for the Chapter:**

> And this wraps up the first part of the story. Thanks a lot for making it this far!
> 
> As I said in the introduction, this chapter is a bit of a mess, and there were a lot of things I wanted to include. And as a result, this chapter just got longer and longer. I hope you still enjoyed it, and thanks a lot for reading this story. I already started writing the next part of the series, and if everything goes well, I'll have the first couple of chapters ready next week.
> 
> I really appreciate any comments and feedback and I hope you'll stick around for the next part!

**Author's Note:**

> Thanks for reading!  
> I wasn't and am still not quite sure how to best structure this, since I sort of published the middle chapter as a one shot already. But I thought that the least confusing way would be to structure it as a series and write a 2-3 chapter prequel before then starting a sequel that takes place after ""the fathers you can't leave behind and the lovers you can't let go".  
> So I guess what I'm trying to say is that feedback is very much appreciated, both on my structural approach and of course more importantly, the work itself!


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